Sodium Hydroxide → (NZ)-N-[(2-phenyl-1,3-thiazol-4-yl)-(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine

HRID 63205Notes

Reaction equation

[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:27][OH:28].[OH-].[Na+]>C(O)C>[C:1]1([C:7]2[S:8][CH:9]=[C:10](/[C:12](/[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[N:27]\[OH:28])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of 1h (210 mg, 0.59 mmol) in 10 mL ethanol was added an aqueous solution (2 mL) of hydroxylamine hydrochloride (127 mg, 1.83 mmol). Then 2 mL 1 N NaOH was added dropwise to the reaction mixture and the mixture was stirred at 55° C. for 3 h. After completion of the reaction, the residue was absorbed on silica gel and purified by column chromatography to give compounds 2e-cis (85 mg) and 2e-trans (50 mg). 1H NMR (300 MHz, DMSO-d6) δ 11.95 (s, 1H), 8.35 (s, 1H), 7.91-7.89 (m, 2H), 7.50-7.44 (br, 3H), 6.85 (s, 2H), 3.73 (s, 6H), 3.70 (s, 3H). MS (ESI) m/z 393.1 (M+Na)+; 368.9 (M−H)−.

Workup

customAfter completion of the reaction
customthe residue was absorbed on silica gel
custompurified by column chromatography
customto give compounds

Sources & evidence

ORD record: ord-197b35234cb948b198f3c1e73c1bcde8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447049B2

Reaction notes

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